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Method of preparing alkyl diselenide

A technology of alkyl diselenide and cycloalkyl, applied in the field of alkyl diselenide, can solve the problems of complex operation, harsh conditions, long reaction time and the like, and achieve the effects of simple post-processing, mild reaction conditions and simple operation

Inactive Publication Date: 2006-01-25
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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Problems solved by technology

In the above method, the reaction of chlorinated hydrocarbons with metal diselenides, or the reaction of selenamides with chlorinated hydrocarbons requires a two-step reaction, and the operation is more complicated and the conditions are harsh.
In addition, aliphatic aldehydes or aliphatic ketones react directly with hydrogen selenide gas, the reaction time is longer, and the toxicity is greater
It is also reported that selenium and sodium borohydride can be prepared without adding organic base (Org. Pre. Pro. Int., 1995, 27, 492-494), but it needs to use strong alkali sodium borohydride
Or react the reactant with selenium, carbon monoxide and water under 30 atmospheres, this reaction time is long, the temperature is high, the yield is not high, and a strong organic base needs to be used in the reaction process

Method used

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  • Method of preparing alkyl diselenide
  • Method of preparing alkyl diselenide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1 2

[0015] The synthesis of embodiment 1 dicyclohexyl diselenide

[0016] Add cyclohexanone (2.5mmol), selenium (2.5mmol), water (2mL), and N,N-dimethylformamide 20ml into a 100ml three-necked flask, and feed it at a rate of 20-60mL / min under normal pressure CO, temperature controlled at 90°C, vigorous magnetic stirring for 7 hours. After the reaction is complete, stop passing CO, cool to room temperature, and stir in air for half an hour, add an appropriate amount of water, extract with ether three times, combine the extracts, and evaporate the solvent under reduced pressure. After passing through the column, the eluent was petroleum ether: ethyl acetate (10:1), and the eluent was concentrated to obtain the product with a yield of 74%, a yellow liquid.

Embodiment 2

[0018] The reaction temperature is room temperature (25° C.), the reaction time is 7 hours, the experimental method and steps are the same as in Example 1, and the yield is 0%.

Embodiment 3

[0020] The reaction temperature was 60° C., the experimental method and steps were the same as in Example 1, and the yield was 46%.

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Abstract

The invention provides a process for preparing alkyl diselenide, which comprises venting and bubbling CO, using fat aldehydes or fat ketones, selenium and water as raw material, and preparing alkyl diselenide through one-step reaction. The invention has the advantages of mild reaction condition, simple operation, no by-product, no need of any adjuvant.

Description

technical field [0001] The present invention relates to the synthesis of alkyl diselenide, which is a process of directly introducing selenium into aliphatic aldehyde or aliphatic ketone. Specifically, the alkyl diselenide is obtained through one-step synthesis under normal pressure and mild conditions. Background technique [0002] Alkyl diselenides are the most widely used organoselenium reagents and important intermediates in organic synthesis. Because it can be converted into a variety of useful organic selenium reagents. For example, it can be reduced to sodium selenide (Tetrahedron, 1986, 42, 5363-5). Sodium selenide is an effective nucleophile, which can undergo various nucleophilic substitution or nucleophilic addition reactions to introduce selenium-containing compounds into the molecule. group; it can also be oxidized by halogen to form an alkylselenide halide, which is an effective electrophile and can undergo a variety of electrophilic substitution or electroph...

Claims

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Application Information

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IPC IPC(8): C07C391/00
Inventor 田丰收陆世维
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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